[28F] For Halloween, my ex-boyfriend had me dress up as Violet Beauregarde from Willy Wonka & the Chocolate Factory so we could roleplay a size / breast expansion scenario [FM]

I can’t tell if this is a wholesome bedroom fantasy for personalities stuck with the whimsy of the 70s classic Willy Wonka & the Chocolate Factory or if it’s just plain weird… but I will leave it to you to decide for the October challenge šŸ˜‚

Maybe as very brief context for those that didn’t grow up with the Roald Dahl classic, Charlie Bucket wins the golden ticket to visit Willy Wonka’s secret, fanciful, magic chocolate factory. The epicenter of the best tasting chocolate in the world and a supposed fantastical production process helmed by the eccentric Willy Wonka. This context is already probably jogging your memory, so I will skip to the punchline. My ex boyfriend for whatever reason had a childhood fascination with one guest in particular that visits the factory, Violet Beauregarde. Violet is portrayed as a rich, bratty, over-the-top competitive character that ends up chewing some experimental bubble gum that inflates her entire body into a giant blueberry. Her skin turns dark blue and she gets rolled around by the Oompa Loompas as her track suit gets stretched to a tiny fraction covering her now expanded body.

I fucked [M]y [F]riend’s younger sister at his birthday party

I made a post a few years ago about hooking up with my best friend’s little sister. That one was pretty long and sad so I thought I’d share a sort of similar story with a happier ending. This one is also pretty friggin long though so be warned.

A friend of mine from college, Rick, invited a bunch of us to go to his younger sister Angie’s farm for his birthday. He does this every year. I was pretty excited because I had a little crush on Angie, who I’d met when she came to visit Rick at college.

Rick is a few years older than me and Angie is closer to my age. She’s got sort of a country-hipster aesthetic going on: big chunky glasses, lots of tattoos, long legs, and a beautiful big ass. We hit it off the first time we met but at that time she had a long-term boyfriend so nothing happened between us. We just flirted a bunch and I left.

[MOD POST] October 2022 Contest

The r/gonewildstories monthly contest will highlight a specific theme for each month. Users can submit their posts for the contest, by tagging it with a special monthly Post Flair. The contest is open for the first 3 weeks of the month. At the end of the 3 weeks, whichever story has the most karma, wins. Contest winners will get a special flair, celebrating their win. And the winning story will be stickied on the top of the Sub for the last week.

All of the Reddit and Sub rules will still apply for the contest. The Mod Team will enforce them, regardless of how well the post is trending.

October 2022 Theme: Costume/CosPlay: Perhaps you were at a Halloween party. Or spiced up the bedroom with some kinky roleplay. Or maybe your partner is into something really specific. Share your gonewildstories version of your adventure, involving costumes or cosplay.

The contest will run from the first of the month to the end of the month. We’ll announce the winner shortly thereafter. So start writing! Remember, proper formatting (please no walls of text) and grammar go a long way to telling a good story. Also, the post still needs to fit the context of r/gonewildstories and follow all of the Reddit and Sub rules.

Upright and Locked [MF]

In the Summer of 1987, I was a broke-ass college graduate who was about to become an even broker-ass graduate student. I had some money in the bank, and I knew that I wasn’t getting any younger, so when an English friend asked me if I’d like to fly home with her, I jumped at the chance.

We had a Row 50ish window and aisle seat on a BA747, flying MIA/LHR. Not ritzy, but not bad either. Pre-9/11 international travel was good stuff, with food and ample free drinks. I was ready to go, seated on the aisle, and dreaming about the verdant English countryside. (Nah, that’s just BS. I was hoping that my friend, who would never be “more than a friend” would maybe become “more than a friend.”)

“I can’t sit in the middle.”

I look up and see this (attractive?) young woman, holding her ticket, puzzled because I am in her seat.

I pull out my ticket, and we compare them.

Yup, same row, same seat.

Before I can call the stewardess, my friend says that I should just sit in the middle. You know, be a gentleman.

[F] Jilling Off To Hubby’s Old Sextapes

Recently, I’ve been desperate to try and find some fun “content” to help me destress and relax after a long day. Still, nothing has really been what I’ve been looking for, leading me to skimming through Hubby’s secret porn collection again. As mentioned in a prior post about my discovery of Hubby’s porn stash, which has numerous videos involving people from our past, the videos I’ve seemed to gravitate around this time are the ones involving Hubby and my former best friend from back when I lived in Australia. There are three videos in the super secret folder, one with them in her room, where she and I had numerous sleepovers. Then two videos in a hotel room that seemed to be from the same night.

I found out my friend [M] 27, jerks off to pics of my g[F], 23 and we became jerkbuds PT 2

This story will be shorter than the first part. I am rock hard right now as I’m typing it to share it with you guys.

So after some months of Jim and I having our fun jerking off to my Sara’s pics, things escalated a tiny bit. We didn’t meet that often, but it had become a thing, we’d do it at least twice a month.

One day we were supposed to meet knowing very well what was gonna happen but Jim told me he had a surprise for me. When we met, I found out the surprise was he had bought a fake vagina in order for us to make our experience a bit more realistic. I personally loved the idea.

So we set up his ipad and we put the fake pussy right in front of it. We had prepared all our favorite pics of my girlfriend and we made a slideshow of them. We looked at the pics, admiring my girlfriend’s beauty as our cocks started to get hard. I honestly had butterflies in my stomach. This time was different. We were actually gonna roleplay sharing my gf.

[M]y childhood [F]riend helped me get over my ex

This one comes from a few years ago when I was nearing the end of my time in college. All through the end of high school and first few years of university, I had the same girlfriend. Ana and I were the super saccharine high-school sweethearts that you normally only see in movies. She was on the swim team, I was on the soccer team, and the two of us maintained genial relationships with almost everyone we interacted with in high school. ā€œPopularā€ is a loaded term, so I won’t say that that’s what we were, but we were definitely well-liked. People were generally rooting for us to live happily-ever-after and we gave them every indication that we would.

That facade persisted through our first couple years in college. I can’t exactly explain why I fell for Ana so hard in high school, but there was something about her that just felt… intoxicating. Like, I was drawn to her in a way that I couldn’t articulate. It was probably her eyes. As much as I appreciate a well-developed physique, there’s something about *eyes* that enchants me, and Ana had these beautiful blue eyes that transfixed me whenever she looked my way.

[MF] I [M34] met an Italian Cougar [F48] on the dancefloor and then spent the entire night drenched in her squirt all over my body ;)

As the title says, yes, this story involves squirting and lots of it. It was with an Italian cougar who I had met at a nightclub.

Until this memorable incident, I thought squirting wasn’t real. Pornstars faked it to get more views. Because until this moment, I never had any of the women I have slept with doing this. So I resigned to the fact that squirting was not real.

So here goes.

It was a Saturday evening, and I was going through a dry spell. No FWBs, no dates, nothing. It was a cold February night. I wanted to break the monotony — so I decided to go watch a late-night movie.

The movie theater was close by, and I had no intentions of going to a club because by the time the movie is over, it will be midnight, and I might be tired.

Anyways, I get ready to go to the movie. As I was heading out the door, for some reason, I thought I should just carry a couple of condoms with me. I didn’t know why. I just did. Maybe it was divine intervention.

3some abroad lets me find out how much of a cuckqueen my GF really is [FFM] + [FM]

“We’re having sex tonight” is always a great start to the evening. My girl is gorgeous, 28, fit & thick. Would be welcome on r/theratio

But it’s been a few weeks, busy with all the bullshit no one comes here to read about, and we haven’t been feeling it. But I’m off for a trip in the morning, she knows I love the girls where I’m headed. So…

“Can’t let you go over there without it. You’ll cum in the first thing that smiles at you”It’s true, for this occasion I’ve got full permission to do whatever I want: because she thinks its hot. It’s not our first time in this space (a threesome where she often watched stands out) but its not like we do the poly thing at home. It’s a bit of a joke to rile each other up, but there’s always in the back of our minds: if it happens, he’ll go for it.We make an easy dinner, we cuddle up, we have lovely cute spooning sex on the couch. ***It’s respectful.*** It’s warm.

Everyone cums quietly, we stumble into bed.